1. Field of the Invention
This invention relates to novel 3-keto-androst-4-ene-17 beta-carboxylic acids, the corresponding androsta-1,4-dienes, the 17 alpha-alkanoyloxy derivatives and the alkyl, phenyl and benzyl 17 beta-carboxylates thereof. More specifically it relates to these compounds which are substituted at the 6 alpha, and 6 beta positions with fluorine. The 17 beta-carboxylates, especially the 17 beta-methyl carboxylates are active anti-inflammatory agents in mammals. The invention further relates to pharmaceutically active compositions comprising an active compound of the invention in combination with a pharmaceutically acceptable excipient.
2. Prior Art
3-Keto-androst-4-ene 17 beta-carboxylic acids which are substituted at the 9 position with chlorine or fluorine and at the 11 position with keto or hydroxy or chloro group are known. See for example U.S. Pat. No. 3,828,080. It is also known that 3-keto-androst-4-ene 17 beta-carboxylic acids may be substituted at both the 9 alpha and 6 alpha positions with fluorine. See for example U.S. Pat. No. 3,636,010. A heretofore unknown series of -3-keto-androst-4-ene 17 beta-carboxylic acids being substituted at the 6 alpha and 6 beta positions with fluorine has been discovered and is disclosed herein. The compounds exhibit good anti-inflammatory activity while exhibiting little adverse systemic activity.